Home > Compound List > Compound details
1200-22-2 molecular structure
click picture or here to close

5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid

ChemBase ID: 51
Molecular Formular: C8H14O2S2
Molecular Mass: 206.32556
Monoisotopic Mass: 206.04352169
SMILES and InChIs

SMILES:
S1SCC[C@H]1CCCCC(=O)O
Canonical SMILES:
OC(=O)CCCC[C@H]1SSCC1
InChI:
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
InChIKey:
AGBQKNBQESQNJD-SSDOTTSWSA-N

Cite this record

CBID:51 http://www.chembase.cn/molecule-51.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
IUPAC Traditional name
lipoic acid
Brand Name
Heparlipon
Biletan
Thioctsan
Synonyms
Lipoate
Thioctic acid
alpha-Lipoic acid
1,2-Dithiolane-3R-pentanoic acid
α-Lipoic acid (alpha lipoic acid)
6,8-Dithiooctanoic acid
DL-6,8-DITHIOOCTANOIC ACID
(R)-6,8-Dithiooctanoic acid
(R)-6,8-Thioctic acid
(R)-(+)-1,2-Dithiolane-3-pentanoic acid
(R)-(+)-1,2-Dithiolane-3-pentanoic acid
Lipoic Acid
(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
(R)-(+)-α-Lipoic acid
(R)-6,8-二硫辛酸
(R)-6,8-硫辛酸
(R)-(+)-1,2-二硫戊环基-3-戊酸
(R)-(+)-1,2-二硫戊环基-3-戊酸
(R)-(+)-α-硫辛酸
CAS Number
1200-22-2
1077-28-7
62-46-4
MDL Number
MFCD01631142
PubChem SID
24881001
160963514
PubChem CID
6112
CHEBI ID
30314
ATC CODE
A16AX01
CHEMBL
134342
Chemspider ID
5886
DrugBank ID
DB00166
KEGG ID
C16241
MeSH Name
Lipoic+acid
Wikipedia Title
Lipoic_acid

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.523468  H Acceptors
H Donor LogD (pH = 5.5) 1.0948822 
LogD (pH = 7.4) -0.6761287  Log P 2.1137793 
Molar Refractivity 54.3714 cm3 Polarizability 21.431002 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.75  LOG S -2.96 
Solubility (Water) 2.24e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Insoluble expand Show data source
Soluble as sodium salt in water expand Show data source
Soluble in ethanol expand Show data source
Apperance
Yellow needle-like crystals expand Show data source
Melting Point
48-52 °C(lit.) expand Show data source
Flash Point
>110 °C expand Show data source
>230 °F expand Show data source
Optical Rotation
[α]/D +115±5°, c = 1% in ethanol expand Show data source
[α]20/D +104°, c = 1 in chloroform expand Show data source
Hydrophobicity(logP)
2.1 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Bioavailability
30% (oral) expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
95+% expand Show data source
97% expand Show data source
Grade
analytical standard expand Show data source
Optical Purity
enantiomeric excess: ≥98.0% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C8H14O2S2 expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals
DrugBank - DB00166 external link
Item Information
Drug Groups approved; nutraceutical
Description A vitamin-like antioxidant. [PubChem]
Indication For nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Neither DMSA nor MSM can cross the blood-brain barrier, which is why both lipoic acid and DMSA are used. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.
Affected Organisms
Humans and other mammals
References
Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [Pubmed]
REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. [Pubmed]
External Links
Wikipedia
Sigma Aldrich - 07039 external link
Analysis Note
identity confirmed by LC-MS
Biochem/physiol Actions
(R)-(+)-α-Lipoic acid was shown to significantly increase pyruvate oxidation while abrogating fatty acid oxidation in rat hepatocytes. These effects make R-(+)-α-Lipoic acid a promising treatment option for the treatment of Type II diabetes. 1
Sigma Aldrich - 579602 external link
Packaging
1 g in glass bottle
MP Biomedicals - 05214667 external link
MP Biomedicals Rare Chemical collection

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. Pubmed
  • • REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle